He said: "I lost a bet over the weekend. I was so sure New England was going to win, that I told a guy who used to be my friend that if New England lost, I would wear a dress on 'Letterman' And so, here I am."
When the host offered the 43-year-old star - who has previously spent time in prison for drink driving offenses - $1,000 to ride the subway in his green dress, cream t-shirt and combat boots, he replied: "Riding the subway would be easier. This I think may be the most humiliating moment of my life - and I've had a couple to choose from. Not looking really butch now, am I?"
Despite his shame, Sutherland - who apologized for embarrassing his family and friends with the outfit - admitted he bought the dress himself, much to the amusement of the sales assistant.
He explained: "You should have seen me shopping for this thing today.
"I walk into a store, and say 'I'm shopping for a big gal, kind of my size, pretty broad in the chest. Do you mind if I try it on?' Then she just said, 'Take it'. I got kind of nervous."
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